Glycosylidene Carbenes. Part 18. Insertion of glycosylidene carbenes into the SnH bond of tributyl- and triphenylstannane: A synthesis of stannoglycosides

Autor:	Daniel Nanz, Eva Bozó, Andrea Vasella, Peter Uhlmann
Rok vydání:	1994
Předmět:	Inorganic Chemistry Anomer Anomeric effect Chemistry Stereochemistry Organic Chemistry Drug Discovery Physical and Theoretical Chemistry Biochemistry Nmr data Catalysis Triphenylstannane
Zdroj:	Helvetica Chimica Acta. 77:1430-1440
ISSN:	0018-019X
DOI:	10.1002/hlca.19940770521
Popis:	Insertion of the glycosylidene carbenes, derived from the gluco- and the manno-diazirines 1 and 2, into the SnH bond of R3SnH (R = Bu or Ph) leads to the fully substituted stannoglycosides 3–8 (53–77%). The 1,2-cis-configurated products are formed preferentially (α-D/β -D ranges from 2.5:1 to 5.1:1 with 1, and 1:1.3 to 1:4.2 with 2). Relative to CH2Cl2, THF favors formation of the equatorial Sn-glycosides. The stannylated (benzyloxy)glucals 9 and 10 were isolated as side products. The reaction of 1 with (Bu3Sn)2 yielded 9 (17% in CH2Cl2; 36% in CCl4) together with the azines 11 and the benzyloxyglucal 12. NMR Data of the Sn-glycosides 3–8 show evidence for an anomeric effect, 1J(C(1),H) being larger in the axial and 1J(Sn,C(1)) larger in the equatorial anomers.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::49483e81c39d9fa86769e8ec8828e179 https://doi.org/10.1002/hlca.19940770521 Zobrazit plný text záznamu Plný text